Organic Structure Challenge

Question

Recently we had this challenge in our Organic Chemistry Department. I was not involved in it but I thought it might be interesting for the SE Chemistry site, so here it is.

Propose a structure for C₂₀H₁₈ with the longest IUPAC name. Following rules apply:

1. Names must be generated with MarvinSketch: Structure>Generate Name…>Preferred IUPAC Name (https://www.chemaxon.com/products/marvin).
2. No isotopic markings can be used.
3. The structures must be possible (no cycles with too much unsaturations nor systems with impossible tension).
4. All the characters will be counted: numbers, letters, points, colons, dashes, everything.
5. Longest name wins.

Here is the example that was given:

and the name provided by MarvinSketch:

(1'R,4'Z,6'Z,8'Z,10'Z,12'S,15'R,16'R,17'R)-spiro[cyclopropane-1,18'-tetracyclo[13.2.1.04,17.012,16]octadecane]-2,2',4',6',8',10',13'-heptaene

141 characters

Good luck and prosperous year 2018!

EDIT

Well, what is a challenge without a prize? So, I have set a bounty worth +50 reputation for the longest name. Sorry, I can not spend much more on it. Remember that you can post more than one structure. If you have proposed one and after some days you find a structure with a longer name, you can post it too.

Answer 1

$\ce{C20H18}$, 246 characters

InChI=1S/C20H18/c1-2-13(1)5-15(13)7-17(15)9-19(17)11-12(19)20(11)10-18(20)8-16(18)6-14(16)3-4-14/h1-4,11-12H,5-10H2/t11-,12+,15-,16-,17-,18-,19-,20-/m1/s1

PIN: (1'R,1''R,1'''R,1''''R,1'''''R,1''''''R,2''''R,3''''S)-octaspiro[tetrakis(cyclopropane)-1,2':1',2'':1'',2''':1''',4''''-bicyclo[1.1.0]butane-2'''',2''''':1''''',2'''''':1'''''',2''''''':1''''''',1''''''''-tetrakis(cyclopropane)]-2,2''''''''-diene

Answer 2

$\ce{C20H18}$, 153 characters

(1'S,2'S,3'R,6'S,8'S)-3'-(cycloprop-2-en-1-yl)-11'-[(cycloprop-2-en-1-yl)methylidene]spiro[cyclopropane-1,7'-tricyclo[6.3.0.02,6]undecane]-2,4',9'-triene

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P. S. I guess someone should just start, so I simply used the slightly modified structure from the example. I'm pretty sure this one is going to be criticized a lot by experienced organic chemists, so it's more like a kick-starter.

I found it very useful to start with Avogadro first to sketch (and optimize, Ctrl+Alt+O) the initial geometry (very handy for the geometries which are distorted or resembling platonic solids), then import cml file to MarvinSketch and do the rest.

For those who would like to check the names, copy it from here, the press Ctrl+Shift+N, Ctrl+V and click Import in MarvinSketch. For the record, currently MarvinSketch 17.29.0 is being used.

Answer 3

$\ce{C18H20}$ : 145 characters

I was curious as to the isomer with the longest name that had actually been reported in the literature rather than hypothetically proposed (so we at least know it exists).

The IUPAC name, whilst not quite as long as some of the examples, is a respectable 145 characters, largely due to the representation of stereochemistry and connectivity.

(2aR,4aR,4bS,6aS,8aR,8bS)-1,2,7,8-Tetramethyl-2a,4a,4b,6a-tetrahydrocyclobuta[a]cyclobuta[2',3']cyclopenta[1',2':3,4]cyclobuta[1,2-b]cyclopentene

The molecule was reported in a 2002 paper (J. Org. Chem. 2002, 67 4436–4440) on the rearrangements of a set of spiro[2.4]hepta-1,4,6-trienes

Answer 4

Here is my input with character count increasing up to down. I have added InChI codes because it seems MarvinSketch is less capable of reading names than it is in their generation.

1. $\ce{C20H18}$: 164 characters

• InChI=1/C20H18/c1-11-3-4-12(2)17-16-9-15-13(11)5-6-14(15)18(17)20(16)10-19(20)7-8-19/h3-6,9,13,15H,1,7-8,10H2,2H3/b4-3-,17-12+/t13-,15+,20-/s2

• PIN: (2'R,4''Z,7''S,11''S)‐3''‐methyl‐6''‐methylidenedispiro[bis(cyclopropane)‐1,1':2',14''‐tetracyclo[8.4.0.0^2,13.0^7,11]tetradecane]‐1''(10''),2'',4'',8'',12''‐pentaene

2. $\ce{C20H18}$: 167 characters

• InChI=1/C20H18/c1-11-3-4-12(2)17-16-9-15-13(11)5-6-14(15)18(17)20(16)10-19(20)7-8-19/h3-8,14-15,18H,2,9-10H2,1H3/b4-3-,13-11-/t14-,15+,18+,20+/s2

• PIN: (2'S,2''R,3''S,7''R,11''R)‐3''‐methyl‐6''‐methylidenedispiro[bis(cyclopropane)‐1,1':2',14''‐tetracyclo[8.4.0.0^2,13.0^7,11]tetradecane]‐1''(10''),2,4'',8'',12''‐pentaene

3. $\ce{C20H18}$: 169 characters

• InChI=1/C20H18/c1-11-3-4-12(2)17-16-9-15-13(11)5-6-14(15)18(17)20(16)10-19(20)7-8-19/h3-6,9,14,18H,2,7-8,10H2,1H3/b4-3-,13-11-/t14-,18+,20+/s2

• PIN: (1''S,2'S,4''Z,6''Z,10''S)‐6''‐methyl‐3''‐methylidenedispiro[bis(cyclopropane)‐1,1':2',14''‐tetracyclo[8.4.0.0^2,13.0^7,11]tetradecane]‐2''(13''),4'',6'',8'',11''‐pentaene

4. $\ce{C20H18}$: 171 characters

• InChI=1/C20H18/c1-11-3-4-12(2)17-16-9-15-13(11)5-6-14(15)18(17)20(16)10-19(20)7-8-19/h3-6,9,13,15H,1,7-8,10H2,2H3/b4-3-,17-12+/t13-,15+,20-/s2

• PIN: (1''S,2'S,4''Z,6''Z,10''R,11''R)‐6''‐methyl‐3''‐methylidenedispiro[bis(cyclopropane)‐1,1':2',14''tetracyclo[8.4.0.0^2,13.0^7,11]tetradecane]‐2,2''(13''),4'',6'',8''‐pentaene

5. $\ce{C20H18}$: 172 characters

• InChI=1/C20H18/c1-11-3-4-12(2)17-16-9-15-13(11)5-6-14(15)18(17)20(16)10-19(20)7-8-19/h3-9,14-15,17-18H,2,10H2,1H3/b4-3-,13-11-/t14-,15+,17+,18+,20+/s2

• PIN: (1''S,2'R,2''S,4''Z,6''Z,10''R,11''S)‐6''‐methyl‐3''‐methylidenedispiro[bis(cyclopropane)‐1,1':2',14''‐tetracyclo[8.4.0.0^2,13.0^7,11]tetradecane]‐2,4'',6'',8'',12''‐pentaene

Answer 5

$\ce{C20H18}$, 290 characters

Heavily based on Daniel Bonniot de Ruisselet's idea, the two "spiraned" cyclopropane pairs next to ending cyclopropenes are fused to bicyclobutanes as well, allowing remaining methyls attachment to the ending cyclopropenes, thus also allowing more chiral centers.

• PIN: (1S,1′R,1′′′S,1′′′′′R,2′′S,2′′′′S,3′S,3′′′S,3′′′′′S,4′R,4′′′R,4′′′′′R)‐2,3′′′′′′‐dimethylhexaspiro[cyclopropane‐1,2′‐bicyclo[1.1.0]butane‐4′,1′′‐cyclopropane‐2′′,2′′′‐bicyclo[1.1.0]butane‐4′′′,1′′′′‐cyclopropane‐2′′′′,2′′′′′‐bicyclo[1.1.0]butane‐4′′′′′,1′′′′′′‐cyclopropane]‐2,2′′′′′′‐diene

• InChI=1S/C20H18/c1-7-3-15(7)9-10(15)17(9)5-19(17)13-14(19)20(13)6-18(20)11-12(18)16(11)4-8(16)2/h3-4,9-14H,5-6H2,1-2H3/t9-,10+,11-,12+,13-,14+,15+,16+,17-,18-,19+,20-

• CXSMILES: [H][C@]12C@([C@@]11C=C1C)[C@]21C[C@]11[C@]2([H])[C@@]1([H])[C@]21C[C@@]11[C@@]2([H])[C@]1([H])[C@@]21C=C1C |c:6,32|

• gzipped and base64 encoded molfile:

  H4sIAGimq1sCA6WWTW7CMBCF9znFXKDW/PlvXSqxocsepIuev7YjGhFPGrBRhODl5WPmeWyxANy+
  fyixAGYOlChy5gv8vZYFOIB4AGwXtfftlXOGL0bEpX5Tp4EywJsXlxVT1dCVuwjv8Iiwr0bxjmLQ
  SlEnXsSk8Bllq0VdDH66lvopySgl5ZpGpfh8kAs/VYtUSijPHuSCZ5TgAno56Yifp/xTy2ku0Qnl
  s1xOKcmhKM92tFFm0t0oM7ObXNQUZ2d3o8zsRimU6FeK5zSYS92NjCuF6KAjfKWjcUoutQj/daSj
  HaWoLRd2iqSjHYkEnqW0NbJPqevzFO+yIK5ThwUzRml72p666ytr5JHvp9RjLtdXzjofmO67sa7W
  GGU76xKPpcttp9FOFVPV3r562SRor3pTDUfe0P9abDf23mSqudkNr61mi0BoqtRVViTDWyTqMyMx
  vXr34s5rq31mFID87hgvagKKvVq8fcfFyEbH1Lj7taAKMQhGZWUeeH08PE4fc6eWdll6tRC0J5R6
  fa+m+uewI2iNYtfFDeDj87L8Autmps9wCgAA
  

(All data according to MarvinSketch 18.23, image postprocessed in a vector image editor; name postprocessed chem.SE and other text editor - RS italicization and apostrophe to prime replacement.
Marvin obviously has some issues, importing the produced InChI string produces some unspecified centers, so I have generated ChemAxon SMILES, this when pasted produces different stereochemistry, so I have added a compressed MDL molfile as well)

Can someone beat 300 characters, by further modifications?

Answer 6

**162 Characters

• PIN:(1'S,2'S,6'S,7'R,12'S,14'S)‐7'‐methyldispiro[cyclopropane‐1,8'‐pentacyclo[7.5.1.02,6.02,14.012,15]pentadecane‐ 13',1''‐cyclopropane]‐2,2'',3',9'(15'),10'‐ pentaene
• I have used MarvinSketch 17.28.0 for generating pin.